Im guilty of romanticizing the Hobopoet life... for I do, in fact, find it romantic. But I should add a caution for those considering a leap into this sort of life: there will be a price.
The price is different for everyone. For some it is loneliness. For some it is poverty. For some it is a loss of status and "respectability". For some it is a loss of comfort. For some it may be all of the above.
Some people hesitate when they realize this. Their illusion of non-stop thrilling adventures and perfect happiness is shattered. Doubt creeps in. Some give up. Some never try to work through the challenges.
But most worthy things have a price. Often, the worth comes from paying that price and accepting it.
And sometimes, by doing so, the challenge is transcended or overcome. And sometimes it is not. As Gandhi said, the reward is in the effort made- not the result.